Nitroalcohols and their preparation are well known. Nitroparaffins or nitroalkanes that contain a hydrogen atom on the alpha carbon enter into condensation reactions of the aldol type to produce nitroalcohols. For instance, nitromethane condenses with propionaldehyde in alkaline solution to give 1-nitro-2-butanol. Tertiary nitroparaffins lack an alpha hydrogen and, therefore, can neither be deprotonated by alkali nor enter into condensation reactions. Preparation of nitroalcohols by condensing aldehydes with nitroparaffins dates back to at least 1900.
An article by Vanderbilt and Hass entitled "Aldehyde-Nitroparaffin Condensation" in Industrial and Engineering Chemistry, Vol. 32, No. 1, January 1940, pp. 34-38, provides some details relating to the preparation of nitroalcohols by condensing a nitroparaffin with an aldehyde in alkaline medium. If the nitroparaffin is secondary, there is only one alpha hydrogen atom which reacts with one mole of an aldehyde whereas if the nitroparaffin is primary, there are two alpha hydrogen atoms which react with two moles of an aldehyde. At middle of p. 35 of this article, preparation of 5-nitro-4-octanol is described whereby 2 moles of 1-nitrobutane, 100 cc of alcohol, and 4 cc of 10N sodium hydroxide solution were initially placed into a flask. Then, 2 mols of butyraldehyde were added slowly to the flask while agitating contents thereof and while maintaining reaction temperature at 30.degree.-35.degree.. Additional aldehyde with water was later added and the solution was allowed to stand 4 days, following which, the alkali was neutralized with hydrochloric acid and the mixture was distilled which yielded 5-nitro-4-octanol. Needless to say, the 4 days it took to prepare the nitroalcohol was excessive and unacceptable for a commercial process.